Cottage vacation rentals in Monticello

Hot Tub, Playground, 3 Acres, and Much More!

Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

Driftwood Cottage on Welcome Lake-peaceful retreat

This gem of a vacation rental is perfectly situated on a private lake. Recently renovated, the main level features an open concept living area, with a cozy fireplace for chilly evenings, upgraded kitchen, a master bedroom with a luxurious en-suite bathroom. A charming loft serves as a cozy relaxation spot or additional sleeping area. Each room offers a spectacular lake view. Two full bathrooms ensures everyone has space to unwind. Outdoor includes a hot tub, perfect for relaxation by the lake.

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK

Private lakefront home with beautiful view, large deck, BBQ grill, and a camp fire pit. Nearby restaurants, shops, hiking trails, concert venue, race tracks, indoor waterpark, and casino. Warm Months: MAY-SEP 3 Kayaks, 2 Paddle Boards, Hot Tub in an under deck privacy nook, 2 Hammocks, Fishing Dock with Deck Chairs, and a Pontoon Boat (for use as 'dock living room' not for boating) Cold Months: NOV-MAR Admire cold/frozen lake from inside, or from the outdoor Hot Tub (with winter wind screen)

Luxury Historic School House Cottage

Step into history inside our freshly renovated 1800s school house home. Relax and take it easy on the expansive front porch, with sweeping views of rural farmland and a historic cemetery next door. Sit by the fire and enjoy a book or beverage with friends and family and cook a nice farmhouse meal. This unique and tranquil getaway won't disappoint. And it's just 4 minutes from Narrowsburg's Main Street. Swimming holes and hiking trails along the Delaware River are just a stone's throw away.

Barton bungalow cozy relaxation on 7private acres

Stay at the Barton Bungalow! This cozy, beautifully renovated bungalow sits on 7 private acres. It has a rustic feel with all the modern amenities. We have high speed WiFi so you can work from home. Enjoy some R&R in the hammock, relax by the fire pit or bbq . We are 2 miles from Walnut Mountain Park and less than 10 miles away from Bethel Woods. Try your luck at Resorts World Catskills or go for a splash at Kartrite indoor water park. The trendy Livingston Manor is less than 20 minutes away

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

Catskills Cozy Retreat:Comfy Beds, Firepit, & More

Experience vintage charm at Jameson Cottage, a mid-century farmhouse-style home surrounded by nature. • Modern amenities and rustic wood finishes. • Gas grill and fire pit. • Two queen bedrooms, open living area, and full bathroom await. • Compact kitchen features beautiful cabinets and open shelves. • Relax in the living room or explore the backyard with its bountiful flora. • Embrace the amenities, unleash culinary creativity, and indulge in the luxury of a clawfoot tub.

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

Lovely Cottage w/ Jacuzzi+Woodstove!

Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Dutchhillcottage, gem in the southern Catskills.

The Dutch Hill Cottage is a renovated, rustic chic design waiting for you and your friends or family to enjoy. Private, comfy & cozy country getaway with amazing views situated on 10 acres of rolling hills in the southern Cattskils, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with amazing suntset views from our huge deck. Plenty of ameneties and we welcome your petdog!

Bella Cottage w/Cozy Fireplace & BBQ, Fall Getaway

Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.